Month: November 2020

13918-92-8, Name is 2,4-Difluorobenzene-1-sulfonyl chloride, 13918-92-8, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step EN-(5-bromo-2-meth enzene- sulfonamide[00299] 2,4-difluorobenzene-1-sulfonyl chloride (6.8 g, 32 mmol) was added into a solution of 5-bromo-2-methoxypyridin-3-amine (6.5 g, 32 mmol) in pyridine (10 mL) and the reaction mixture was stirred at r.t. for 20 hours before the reaction solution was concentrated to dry in vacuo to give a crude product which was purified with column chromatography (EtOAc : Petroleum ether = 1 :2 as eluent) to give the product as a brown solid (10 g, 83%). 1 H-NMR (300 MHz, DMSO-d6), delta 10.46 (s, 1 H), 8.52 (s, 1 H), 7.80-7.72 (m, 2H), 7.56 (m, 1 H), 7.20 (m, 1 H), 3.62 (s, 3H). LC/MS, ESI, m/z, 379, 381 (m+1 )+, Br pattern found.

Statistics shows that 2,4-Difluorobenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 13918-92-8.

Reference:
Patent; GLAXOSMITHKLINE LLC; BOTYANSZKI, Janos; DICKERSON, Scott Howard; LEIVERS, Martin Robert; LI, Xiaofei; MCFADYEN, Robert Blount; REDMAN, Aniko Maria; SHOTWELL, John Bradford; XUE, Jianjun; WO2012/174312; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 24279-39-8, name is 2,6-Dichloro-4-(trifluoromethyl)aniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 24279-39-8, 24279-39-8

REFERENCE EXAMPLE 3 Nitrosyl sulphuric acid, prepared from sodium nitrite (69 g, 1 mol) and concentrated sulphuric acid (600 ml) was added dropwise with stirring to a cooled solution of 2,6-dichloro-4-trifluoromethylaniline (230 g, 1 mol) in glacial acetic acid (1250 ml) at 15-20 C. The mixture was stirred for 1 hour at ambient temperature. The diazonium mixture was run slowly into a solution prepared from cuprous bromide (143.4 g, 1 mol), hydrobromic acid (48%, 1 l) and ice (approx. 1000 g) at a rate so as not to exceed a temperature of 35 C. After 1 hour the mixture was steam distilled to give 1 l of distillate which was diluted with water (3 l) and extracted with diethyl ether (2*500 ml). The organic fractions were combined and washed with aqueous sodium hydroxide solution (2M, 2*250 ml) and water (250 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The oily residue was distilled to give 1-bromo-2,6-dichloro-4-trifluoromethylbenzene (256.8 g) as a colourless liquid, b.p. 74-78 C. at 6 mmHg.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,6-Dichloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; May & Baker Limited; US5206257; (1993); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 13526-66-4

Example 70(?)-2-(1-(3-((1 -Methyl-1 H-indazol-5-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene) hydrazinecarboxamide(6-Chloroimidazo[1 ,2-b]pyridazin-3-yl)(1 -methyl-1 H-indazol-5-yl)methanol (70.1)To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1.00 mmol) in 5 ml_ THF, was added ethylmagnesium bromide (1.50 ml_, 1.50 mmol) at -10 0C. After stirring at – 10 0C for 1 hour, 1 -methyl-1 H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to room temperature slowly and stirred for additional 2 hours. The reaction was quenched with Sat. NH4CI solution and concentrated under reduced pressure. The residue was diluted with water, and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 98577-44-7, name is 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane, molecular formula is C5H6Br2Cl2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 98577-44-7.

Tricyclo [1.1.1.01’3] pentane Methyllithium (46.3 mL, 74.1 mmol, 1.6M in diethyl ether) was added to a solution of l,l-dibromo-2,2-bis(chloromethyl)cyclopropane (10 g, 33.7 mmol) in pentane (10 mL) stirred at -78C for 15 min. After the reaction mixture was maintained at -78C for 15 min, the reaction flask was removed from the dry ice/acetone bath and placed in an ice-water bath. The reaction mixture was stirred at that temperature for 2 hrs. The volatiles, which was warmed at 40C by using an oil bath, were collected via a shortpath distillation condenser under a dry-ice-acetone environment. The condensed material was used in next reaction without further purification.

The synthetic route of 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; EASTMAN, Kyle J.; PARCELLA, Kyle E.; WO2014/159559; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, Adding a certain compound to certain chemical reactions, such as: 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13526-66-4.

[00359] EX. 8-29 free base and hydrochloride salt were prepared in 50 g scale according the following procedures. D [00360] To a solution of 3-bromo-6-chloroinnidazo[1 ,2-b]pyridazine (150 g, 0.65 mol) and 3-(trifluoromethyl)phenylboronic(143 g, 0.65 mol) in dioxane/H2O(2.5 L: 4:1 ) was added K2CO3 (180 g, 1 .3 mol) and Pd(PPh3)4 (10 g, 10 mmol). The mixture was stirred at 80 C for 24 h. The solution was concentrated, partitioned with EA/H2O. The aqueous layer was extracted with EA (500ml_) for 3 times. The collected organic layers was dried over Na2SO , concentrated and purified by column chromatograph (PE:EA, 3:1 to 2:1 ) to give 6-chloro-3-(3-(trifluoromethyl)phenyl)imidazo[1 ,2-b]pyridazine (135.15 g, 70.3%) as yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

432-21-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 432-21-3 as follows.

1-Chloro-3-iodo-2trifluoromethyl-benzene; To a suspension of 3-Chloro-2-trifluoromethyl-phenylamine (121.61 g, 0.622 mol) in water (356 mL) was added 37% aqueous HCl portionwise allowing reaction temperature to rise to 42 C. The mixture was stirred for 30 minutes then cooled with ice/MeOH bath to 5 C. DCM (40 mL) was added and the mixture was stirred for 10 minutes. A solution of NaNO2 (53.52 g, 0.776 mol) in water (99 mL) was added dropwise while keeping the temperature of the reaction mixture below 5 C. After complete addition, the reaction mixture was stirred for 30 minutes and a solution of NaI (110.98 g, 0.740 mol) in water (198 mL) was added dropwise while keeping the temperature of the reaction mixture below 5 C. After completion of the addition, the reaction mixture was stirred for 1 hour and 15 minutes, and DCM (0.79 L) was added followed by NaHSO3(35.92 g) to discharge iodine color. The organic layer was washed (brine), and the water layer was sequentially reextracted (2¡Á0.2 L DCM). The organic layers were dried (Na2SO4), combined, and the volatiles were evaporated. The residue (180.55 g) was purified on 0.8 kg of silica gel (elution with 4 L of cyclohexane). The fractions were analyzed by GC, and those having more than 80% of the product were combined, and the volatiles were evaporated. The liquid residue was placed in the freezer for 1 hour, after which the solids were filtered, washed (pentane) and air-dried to afford 78.84 g (41%) of the desired product as beige solid in several crops (97-98% GC purity with 1H and 19F NMR’s clean and consistent with the desired product). The mother liquors were purified on 0.8 kg of silica gel (eluting with 4 L of cyclohexane). The fractions were analyzed by GC, and those having more than 80% of the product were combined and the volatiles were evaporated. The liquid residue was placed in the freezer for 1 hour, and solids were filtered, washed (pentane), and air-dried to give an additional 31.56 g (17%) of the 1-Chloro-3-iodo-2-trifluoromethyl-benzene as white solid (96% GC purity with 1H and 19F NMR’s clean and consistent with the desired product). Also, additional product was obtained (14.30 g, 8%, 81% pure GC) from mother liquors and 28.82 g (50% by GC, froim the less pure fractions. GC analysis done on a DB5 Column, 30 meters, 0.32 mm id, 0.25 um film, 75-300 C., 15 C./min., Injector temperature: 275 C., Detector temperature: 350 C., Retention time: 3.88 minutes. MS: APCl: M+: 306.0 (305.9)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 432-21-3, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US2008/167319; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life. 13526-66-4

75. 2-(trans-4-((3-(3-fluorophenyl)imidazof1,2-blpyridazin-6- yl)amino)cvclohexyl)propan-2-ol (EX. 8-75) [00463] To a solution of 3-bromo-6-chloroinnidazo[1 ,2-b]pyridazine (500 mg, 2.15 mmol) in a mixed solvent of dioxane (5 ml_) and water (0.5 ml_) was added (3-fluorophenyl)boronic acid (273 mg, 1 .96 mmol), K2CO3 (81 1 mg, 5.88 mmol) and Pd(dppf)2Cl2 (79 mg, 0.098 mmol). The reaction mixture was stirred at 80C overnight under N2. TLC (PE: EA = 5:1 ) showed the starting material was consumed. The mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc = 20:1 to 1 :1 ) to give 6-chloro-3-(3-fluorophenyl)imidazo[1 ,2-b]pyridazine (300 mg, 56%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 13526-66-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 2533-69-9.

2-Cyano-5-[2-chloro-4-(trifluoromethyl)phenoxy]-benzimidazole was prepared from 4-[2-chloro-4-(trifluoromethyl)phenoxy]-1,2-diaminobenzene as described below: To a solution of 4-[2-chloro-4-(trifluoromethyl)-phenoxy]-1,2-diaminobenzene (35 g; 0.122 mole) in acetic acid (165 ml), methyl trichloroacetimidate (15.1 ml; 0.122 mole) is added.

The synthetic route of Methyl 2,2,2-trichloroacetimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Agrochimie; US4622323; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

932-96-7, Adding a certain compound to certain chemical reactions, such as: 932-96-7, name is 4-Chloro-N-methylaniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 932-96-7.

General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2¡Á) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.

According to the analysis of related databases, 932-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khanfar, Mohammad A.; Quinti, Luisa; Wang, Hua; Choi, Soo Hyuk; Kazantsev, Aleksey G.; Silverman, Richard B.; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 414 – 426;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1996-29-8, 1996-29-8

EXAMPLE 13 (3R,4S)-4-(4′-Chloro-2′-fluorobiphenyl-4-yloxy)-1-pyridin-3-yl-pentan-3-ol Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.20 g, Example 11)), 1-bromo-4-chloro-2-fluorobenzene (0.21 g), 2M aqueous sodium carbonate (0.57 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in toluene (5 ml) and ethanol (2 ml). The reaction mixture was heated at 100 C. for 4 hours. After cooling, the solution was concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml) and the suspension was stirred at room temperature for 6 hours. After work up, the residue was purified by normal-phase HPLC eluding with a gradient of 0-25% ethanol in dichloromethane to give an oil (0.13 g). MS (APCI) 386 (M+H)+ 1H-NMR(CDCl3) 8.51(1H,d); 8.45(1H,dd); 7.56-7.54(1H,m); 7.43(2H,dd); 7.33(1H,t); 7.26-7.15(3H,m); 6.94(2H,d); 4.41-4.37(1H,m); 3.87-3.86(1H,m); 3.0-2.95(1H,m); 2,80-2.75(1H,m); 2.15(1H,d); 1.87-1.84(2H,m); 1.31 (3H,d).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-4-chloro-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US6300352; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics